Boston Celtics Acquire Jrue Holiday To Complete Successful Offseason

Just 24 hours before media day and the beginning of training camp, the Boston Celtics have put a bow on their busy offseason.

It appears the final (major) piece was acquiring veteran guard Jrue Holiday from the Portland Trail Blazers, less than a week after Holiday was involved in the larger three-team deal sending Damian Lillard to the Milwaukee Bucks.

In an effort to shore up their perimeter defense and counter Milwaukee’s latest move in a wide-open Eastern Conference, the Celtics had to ship guard Malcolm Brogdon and center Robert Williams to Portland. It also cost them a 2029 unprotected first-round pick and the Golden State Warriors’ 2024 first-round pick, which the Celtics obtained in the Marcus Smart trade that kicked off this summer.

Boston now has four players above the $30 million salary figure, per Yossi Gozlan of CapSheets.com. This launches them to $214 million in combined contracts and estimated luxury tax penalties. Holiday is now officially their most expensive player until Brown’s super-max kicks in next year:

Note: This was before the Celtics agreed to a training camp deal with center Wenyen Gabriel.

This trade doesn’t totally empty Boston’s cupboard of draft capital, either. Technically, they still own two future first-round picks, eight second-rounders, and potential pick swaps that can be used in additional deals. However, if they elected to shore up their depth with another trade, it would be next to impossible to match salaries for anyone in the mid-level exception range without including either Al Horford’s $10 million or Derrick White’s $18.3 million. In simple terms: They will likely need to find cheaper options and fringe rotation guys, as Horford and White are too valuable for their desired playstyle and defensive strengths.

Shortly after the big news of the day, Boston agreed to terms with free agent Wenyen Gabriel. Per Shams Charania, he will join the Celtics on a training camp deal with a chance to make the final roster. Gabriel played 68 games for the Los Angeles Lakers last year, spending 78% of his minutes at center and 22% at the four. As a very switchable defender and efficient screen-and-roll option (shooting 64.7% from inside the arc with the Lakers) he’ll be another athletic body that elevates Boston’s versatility.

For the Celtics, the swing for Holiday is a win-now maneuver that focuses on the 2023-24 championship run. It’s also a gamble on perimeter containment making up for the lack of aggression and youth they have roaming the paint. More than anything, Boston is banking on healthy seasons from Kristaps Porzingis and Al Horford, which would mitigate the blow from sending arguably their most important defender (Williams) out the door.

But any way you slice it, they were going to have availability concerns. Williams was only on the court for 35 games last year, less than 43% of the regular season. Over the last two years, he’s battled knee and hamstring issues that have plagued the Celtics in critical stretches. He had surgery on his left knee before last year’s training camp, which kept him sidelined until mid-December.

It’s worth pointing out: Boston was 33-14 in the games Williams missed last season — a winning percentage of .702, equivalent to a 58-win pace.

Of course, nobody should claim Williams didn’t make a difference. When healthy, he gained the trust of everyone on the floor with his supreme rim-protection and ability to clean up his teammates’ mistakes. As a backline roamer and outstanding helper on drives, it gave Tatum, Brown, and Smart more leeway to get aggressive on the ball. If any of them got roasted off the dribble, one of the most reliable defenders in the league could at least put out the fire.

On a per-minute basis, Williams was a driving force to success and precisely the kind of player any coach would love to have as a security blanket. During the 2022 Finals, Al Horford mentioned how comfortable he and his teammates felt while making weakside rotations, knowing Williams would be in position to ‘help the helper.’

But, it become hard for the Celtics to rely on his health. As a result, head coach Joe Mazzulla had a difficult time finding the right lineup combinations when his center could rarely stay on the floor. By the time the postseason arrived, the team shuffled between their traditional/two-big lineups and the five-out configuration that gave their stars more offensive firepower.

In an ideal world for Stevens, he would’ve addressed the point-of-attack defense without moving on from his 26-year-old center that continues adding impact and individual talent each summer. When most of your team’s salary cap is accounting for the Tatum-Brown-Porzingis trio ($100.4 million this season), it’s nothing short of a blessing to have your best defender as the sixth-highest paid player in a loaded rotation.

The NBA universe doesn’t work that way, though. To obtain All-Star, championship-winning services … teams must pay an adequate price.

This trade signals Boston is not only comfortable banking on Porzingis’ health after playing 65 games last year, but they left themselves with no choice. They massively increased their talent in the main rotation, trading for a 7’3” sharpshooter that will have opportunities to bend defenses in a way this team has never had. Porzingis has made 40% of his perimeter attempts from 27 feet extended, the 12th-highest mark in history among players to shoot at least 50.

Porzingis is also a skilled paint protector when he’s actually playing with guards that aren’t turnstiles. The Celtics will undoubtedly try different coverages throughout the year, but Porzingis and Holiday as a drop-coverage tandem will be a beauty to watch. Holiday is one of the greatest ‘rearview contest’ defenders of this era, fighting over screens and funneling his man to the rim-protecting big man waiting inside. (Crazily enough, White probably isn’t far behind him on that list).

Things will have to break right for Boston to put it all together. By losing Williams, they need to preserve Horford, who just turned 37, by lowering his responsibility during the long season. Mazzulla will try different starting units depending on matchups, but for the most part, their best option might be starting White-Holiday-Brown-Tatum-Porzingis, while Horford fills a bench role. If that leaves Boston too small for rebounding and interior defense, they might have to explore the market for more size. The worst-case scenario would be relying too heavily on Horford and his body breaking down before a playoff run.

For all of the frontcourt concerns, though, this should be obvious: Jrue Holiday is worth those potential headaches. Not only is he among the most unselfish, team-first personalities across the league — but there’s no other guard who matches his combination of defensive IQ and offensive capabilities. This isn’t a specialist, who has only earned his money by being a nuisance and disrupting guys with his defense. It’s an All-Star at the tail end of his prime, who recently played a monumental role in helping Giannis and the Bucks finally break through the wall.

Holiday is coming off one of his most impressive offensive seasons, too. In 67 games, he averaged 19.3 points and 7.4 assists on efficient shooting splits of 54.2% from two, 38.4% on threes, and 85.9% at the foul line. With Khris Middleton out of the lineup for a large portion of last year, the Bucks needed Holiday to increase his usage and become more than just a play connector — his scoring acumen and playmaking chops carried a higher responsibility for a Milwaukee unit that still finished No. 1 in the East despite injuries. While Giannis Antetokounmpo’s MVP-caliber season was the primary reason for it, they don’t sniff 58 wins without Holiday’s brilliant two-way expertise.

Among the biggest and most important changes Holiday demonstrated last year was tweaking his shot profile and tapping back into the facilitator role he seemed to deviate from in Milwaukee. His three-point volume jumped to 6.8 attempts per 36 minutes and 40.2% of his overall shot distribution — both career high numbers. While the efficiency took a slight dip from 41.1% to 38.4%, that’s often a sacrifice teams are happy to make when starved for creation. As a playmaker, Holiday’s assist percentage rose to 34.4%, his highest figure since 2016-17 in New Orleans. It was still accompanied by a diet of puzzling turnovers and errors, but again, the Bucks weren’t operating under ideal circumstances in the halfcourt — Middleton, a huge component of their pick-and-roll sets, missed 49 games with knee problems.

This summer was a form of guard consolidation for the Celtics, who essentially swapped the Smart and Brogdon tandem for a Holiday and Porzingis pairing. Brogdon proved to be a successful regular season addition to last year’s Celtics, as he captured the Sixth Man of the Year award and shot the leather off the ball for most of the season. It was evident Boston was shopping him in the trade market all summer, though, and that likely could’ve been related to his durability concerns.

By acquiring Holiday at the expense of both Smart and Brogdon, it paves the way for Derrick White to get even more minutes — perhaps the biggest ‘win’ of the offseason for Boston. Nobody should envy the opponents having to deal with the peskiness of both White and Holiday, particularly in the same lineup, on a nightly basis. The elite screen navigation, ability to stay attached to the hip of any ball-handler, and unmatched defensive intelligence — knowing when to leave their feet, when to use their hands, and how to handle physical matchups — will be the leading causes of nightmares in the East.

Holiday is an unequivocal upgrade in Smart’s former role. He’s a more efficient shooter, a more skilled shot creator, and the most intelligent, respected defender in the league with the most positional versatility. From point guards to seven-foot power forwards, there’s yet to be a player Holiday has backed down from. He might not win every war — Jimmy Butler is probably still shouting at him, even while complaining about gas prices — but he’s always going to force his opponent to exert as much energy as possible.

Both Kevin Durant and Paul George have said, on the record, that Holiday is the fiercest and most talented defender they’ve faced.

As Boston fans surely noticed last year, Smart regressed a bit as an individual defender after being a menace during the 2021-22 campaign. Sure, he’s four years younger than Holiday, but the Celtics are betting on more productive and offensively-polished player stepping into those minutes to help give their team a stronger threat, without losing any of the grit and hustle that made Smart so beloved in the city.

The TD Garden audience is no stranger to Holiday’s impact in a pivotal playoff game:

At 33 years old, Holiday still has some juice left in the tank. As Wojnarowski reported, the Celtics are determined to keep Holiday with their core long-term. In guaranteed years, Holiday only has this upcoming season left on his contract, worth $34.9 million. But if he and the Celtics are eager to stick together, Boston will have a chance to offer him an extension. In terms of extension options, both parties will have to discuss a few different scenarios.

Holiday will become extension-eligible on February 22, but will only be able to extend for two seasons. Another option would be to wait six months from today, as Holiday would be able to add four years to any extension.

If he and his camp elect to wait until free agency, Holiday could accept his $39.4 million player option for 2024-25, then sign an extension with Boston.

Considering his age, the Celtics will likely want to get something on paper in late February or early March, just so they wouldn’t have to commit too many years. As always, it will come down the player’s preferred route.

That’s for a later discussion, though, as Holiday can’t legally extend until the All-Star break.

For now, it’s all about the Celtics’ management not getting complacent with their roster. They had an opportunity to run it back with the pieces that helped them become a perennial East powerhouse. It would’ve been easy to fall in love with a team that reached three Conference Finals in four years, including a trip to the NBA Finals where they came a few Curry flurries away from raising an 18th banner.

This offseason was clearly dedicated to retaining Brown and reshaping the pieces around their young wings. By adding Holiday to the mix, they become the most talented playoff rotation in the league. As training camp opens, the focus will shift to Mazzulla and his new coaching staff to put the proper system in place, define everyone’s role, and become a deadlier version of what opponents saw last year.